Toluene → Diphenylamine

Participants

Reaction Steps

The toluene solution of the sulfenyl chloride was added to the THF solution of the diphenylamine sodium salt. The reaction mixture was stirred cold for 1 hour, cooling was removed and the reaction was stirred an additional hour. The reaction mixture was filtered through celite and solvent was removed in vacuum leaving a brown oil. Chromatography on silica gel yielded the desired product as a yellow oil which solidified on trituration with hexanes (m 109°-122° C.).

Provenance & Evidence